Today I’ve rounded up 9 dressy casual spring outfits! I don’t know about your spring, but ours is always packed with lots of events! From Easter to both Benson’s and my birthdays, to lots of friend’s birthdays, baby showers, etc., there seems to be a lot of times when I need a dressy-casual outfit.
What is Dressy Casual?
Dressy-casual is what I call casual looks with jeans or comfy jersey dresses that are usually a bit too dressed up for running a ton of errands or spending a long time with kids. These are the kind of outfits I wear out to lunch with friends, going to dinner sans kids to celebrate a friend’s birthday, to church, or even just for a day when I’m out and about in meetings and want to dress a step up from jeans and a cotton tee.
If you’re interested in the building blocks for a dressy-casual wardrobe, check out my recent post on that HERE. Onto the outfits!
SIZING INFO: I’m 5’6″ and usually size 6/8 or S/M in clothes and 8.5 to 9 in shoes.
I’ve worn this top on repeat since getting it because it’s one of the few dressy casual pieces I have that fits at 37+ weeks pregnant. ??? This top is simple enough to go with a lot of things, but the detailed sleeves and material dress it up. Pairing it with a statement necklace and peep toe booties steps it up a notch too, making it my go-to dressy casual look these days.
I wore this last week to a gathering for female entrepreneurs and creatives. It was a casual atmosphere, but of course for being around a bunch of creative women, I wanted to look a little more dressed up! I’ve also worn it to church and to a lunch date with Benson. Like I said, it’s my go-to dressy casual outfit these days!
Shop for the Look:
Top: c/o ModCloth (exact–size M)
Jeans: Macy’s (exact maternity–size S; exact fave NON-maternity–size down to 4)
Shoes: Target (exact–size 9)
Necklace: Nordstrom (similar)
Bag: c/o ModCloth (exact)
I wore this to our church’s Easter service this past Sunday, and while it’s not a maternity dress, it is SO.DANG.COMFY. at 37 weeks pregnant! WAY comfier than jeans! Sunday was also Benson’s birthday, and I also wore this to celebrate at all-you-can-eat Korean BBQ. And I didn’t stay in the dress because it was a nice restaurant–Benson, my sister-in-law, and my brother were all in athleisure. I wore the dress because when it’s all you can eat Korean BBQ, stretchy clothes are required!!!
This dress is sold out in most sizes, but you should request to get notified and for it to come back in stock HERE. I’ve seen it restocked once already, which is how I snagged it. But there are also a couple of similar options that I’m nearly positive will be equally as comfy: THIS and THIS.
Shop for the Look:
Dress: c/o ModCloth (exact–size M; similar, similar)
Jacket: Old Navy (similar, similar)
Bag: Nordstrom (exact)
Shoes: Old Navy (similar; similar cheaper wedges)



Top: J.Crew Factory (updated version in other colors; similar )
Jeans: LOFT (exact–I wear size 28 Petite for ankle length)
Bag: Nordstrom (exact)
Shoes: Old Navy (similar; similar cheaper wedges)
Necklace: c/o Dear Mushka (exact)
Dress: Old Navy Maternity (short sleeve in other prints; non-maternity in other prints)
Jacket: Old Navy (similar, similar)
Bag: Nordstrom (similar)
Necklace: Nordstrom (similar)
Earrings: c/o Nickel & Suede (exact–size M)


Top: c/o ModCloth (exact–wearing size L; similar)
Cardigan: Old Navy (exact–size M)
Jeans: Nordstrom (updated exact version–size 8 for looser thighs)
Shoes: Old Navy (similar; similar cheaper wedges)
Necklace: c/o ModCloth (exact)
Bag: c/o Modcloth (exact)


Top: J.Crew Factory (exact–updated version)
Jacket: Macy’s (similar, similar)
Jeans: Nordstrom (similar–my fave pair, I size down to 4)
Shoes: Old Navy (similar, similar)
Bag: Sole Society (similar, similar)
Necklace: H&M (similar but brighter)
This is one of the few outfits in this post with a softer knit kinda top. It can be worn casually but can also be dressed up because it drapes differently than a standard cotton t-shirt plus has a pretty print. I’ve worn it in a casual outfit with denim jeans and sandals, but pairing it with jewelry and pointy toe flats like in the outfit above dresses it up more.
Shop for the Look:
Top: c/o White Plum (similar, similar, similar)
Cardigan: Nordstrom (exact–wearing XS, similar)
Jeans: Old Navy Maternity (exact–wearing size 6; exact non-maternity–I wear size 6; similar non-maternity–I wear size 6)
Shoes: Amazon (exact–wearing size 9; similar)
Necklace: Nordstrom (similar)
Watch: c/o JORD (exact)
This is another outfit from last spring that I still like a lot. A moto jacket is one of my go-to completer pieces to finish dressy-casual looks.
These lace up booties are from Target last year, and they are a knock-off of this very expensive pair by Jeffery Campbell. However, I found a similar cheaper pair for under $40 in a few sizes HERE!
Shop for the Look:
Top: c/o ModCloth (similar) (similar)
Jacket: Macy’s (similar, similar)
Jeans: Old Navy (similar)
Shoes: Target last year (similar, similar designer pair that’s super expensive!)
Necklace: c/o Dear Mushka (exact)
These types of tops are my dressy-casual g0-tos both when I’m not pregnant and during pregnancy. I have talked about the longer version of this Lush tunic in white, saying it’s one of my most remixable pieces. (See it worn 10 ways HERE.) I have this shorter version in olive and black. They are all really effortless to wear and honestly I feel like their loose fit makes them more comfortable than a cotton tee.
My top hasn’t been available for several years, but there is a similar one at Kohl’s HERE. See the ways I’ve worn this olive tunic HERE. I looove it brightened up for spring with white jeans and light blue and turquoise accents!
Shop for the Look:
Top: Nordstrom (similar in Urban Olive)
Jacket: Old Navy (similar, similar)
Jeans: Old Navy Maternity (exact–wearing size 6; exact non-maternity–I wear size 6; similar non-maternity–I wear size 6)
Shoes: Nordstrom (exact, exact)
Bag: Nordstrom (exact)
There you go, 9 dressy casual outfits you can try this spring!